5-Methyl-hept-3-en-2-one → 3,6-Dimethyl-oct-1-yn-4-en-3-ol

HRID 68014Notes

Reaction equation

HRID 68014 reaction equation
[CH3:1][CH:2]([CH2:8][CH3:9])[CH:3]=[CH:4][C:5](=[O:7])[CH3:6].[C:10]([Mg]Cl)#[CH:11]>O1CCCC1>[CH3:6][C:5]([OH:7])([CH:4]=[CH:3][CH:2]([CH3:1])[CH2:8][CH3:9])[C:10]#[CH:11]

Participants

4

Reactant 2

HCID 1384125-Methyl-hept-3-en-2-oneHCID 178462451HCID 178462451, compound

Product 1

HCID 536333433,6-Dimethyl-oct-1-yn-4-en-3-olYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

126 g (1 mole) of 5-methyl-hept-3-en-2-one are added in the course of 1 hour, with stirring, to 1 liter of a 1.1 molar solution of ethynyl-magnesium chloride in tetrahydrofuran, at 10° C. After allowing about a further hour for reaction, the mixture is worked up similarly to Example 1. 126 g of 3,6-dimethyl-oct-4-en-1-yn-3-ol, of boiling point 41° C./0.05 mbar and nD25 =1.4514, are obtained. This corresponds to a yield of 83% of theory. Scent: woody, herbal, fatty.

Workup

  1. customAfter allowing about a further hour for reaction

Sources & evidence

ORD record
ord-b82967f317024464ba9126b17749a594
Source dataset
uspto-grants-1982_08
Patent number
US04347388

Reaction notes

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